Potassium Phosphate, Tribasic → HCID 67283370, compound

HRID 407835Notes

Reaction equation

HRID 407835 reaction equation
Br[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8].[CH2:10]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH2:19][CH3:20])[C:13]=1B(O)O)[CH3:11].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:19]([C:14]1[CH:15]=[C:16]([CH3:18])[CH:17]=[C:12]([CH2:10][CH3:11])[C:13]=1[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8])[CH3:20]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 110954262-Bromo-3-methoxycyclopent-2-enoneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57437319(2,6-Diethyl-4-methylphenyl)boronic acid

Product 1

HCID 67283370HCID 67283370, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred suspension of 2-bromo-3-methoxycyclopent-2-enone (17.5 g, 91.6 mmol), 2,6-diethyl-4-methylphenyl boronic acid (26.4 g, 137 mmol) and freshly powdered potassium phosphate (38.9 g, 183 mmol) in anhydrous, degassed toluene (450 ml) under a nitrogen atmosphere are added palladium (II)acetate (0.411 g, 1.83 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.51 g, 3.67 mmol). The reaction mixture is heated at 90° C. for 6.5 hours and then allowed to cool to room temperature overnight. The reaction is diluted with water (400 ml) and extracted with ethyl acetate (3×150 ml). The combined organic extracts are washed with brine (50 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to dryness under reduced pressure to give a brown oil. The crude product is purified by column chromatography on silica gel to give 2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone.

Workup

  1. customdegassed toluene (450 ml) under a nitrogen atmosphere
  2. temperatureto cool to room temperature overnight
  3. extractionextracted with ethyl acetate (3×150 ml)
  4. washThe combined organic extracts are washed with brine (50 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate is evaporated to dryness under reduced pressure
  8. customto give a brown oil
  9. customThe crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9bcaf4a699714bf6b4da1e95b6e4a700
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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